Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides

doi:10.6023/cjoc201810025

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1489-1496.DOI: 10.6023/cjoc201810025 Previous Articles Next Articles

Notes

新型N-取代苯基-2-吡唑基烟酰胺类化合物的合成及其生物活性

尚俊峰, 刘巧霞, 王宝雷, 李正名

南开大学化学学院元素有机化学国家重点实验室化学化工协同创新中心(天津) 天津 300071

收稿日期:2018-10-19 修回日期:2018-12-03 发布日期:2019-01-18
通讯作者: 王宝雷, 李正名 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
基金资助:
国家重点研发计划（Nos.2017YFD0200505，2018YFD0200100）、国家自然科学基金（No.21772103）和天津市自然科学基金（No.17JCYBJC19900）资助项目.

Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides

Shang Junfeng, Liu Qiaoxia, Wang Baolei, Li Zhengming

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071

Received:2018-10-19 Revised:2018-12-03 Published:2019-01-18
Contact: 10.6023/cjoc201810025 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
Supported by:
Project supported by the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100), the National Natural Science Foundation of China (No. 21772103) and the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900).

Based on the agrochemical structure of anthranilic diamides, fourteen novel N-substitutedphenyl-2-pyrazolyl- nicotinamides were conveniently synthesized with 2-chloro-3-cyanopyridine and 4-bromopyrazole or 3,5-dimethylpyrazole as starting materials, via an "acyl transposing" design strategy. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay tests indicated that most of these compounds exhibited obvious insecticidal activity at the test concentration of 200 mg/L, among which N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)-2-(3,5-dimethyl-1H-pyra- zol-1-yl)nicotinamide (Il) possessed a 70% mortality rate against Mythimna separata Walker; some of the compounds displayed favorable fungicidal activities at 50 mg/L towards Physalospora piricola and Alternaria solani Sorauer, especially 2-(4-bromo-1H-pyrazol-1-yl)-N-(2-(cyclopropylcarbamoyl)-4-iodo-6-methylphenyl)nicotinamide (If) and 2-(4-bromo-1H- pyrazol-1-yl)-N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)nicotinamide (Ih) against Physalospora piricola, and 2-(4- bromo-1H-pyrazol-1-yl)-N-(4-chloro-2-(propylcarbamoyl)phenyl)nicotinamide (Id) against Alternaria solani Sorauer had growth inhibitory rates of 62.9%, 54.3% and 54.5%, respectively. These research results provide important reference for the further study of novel 2-pyrazolylnicotinamide derivatives.

Key words: 2-pyrazolylnicotinamides, synthesis, insecticidal activity, fungicidal activity

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Shang Junfeng, Liu Qiaoxia, Wang Baolei, Li Zhengming. Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides[J]. Chin. J. Org. Chem., 2019, 39(5): 1489-1496.

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新型N-取代苯基-2-吡唑基烟酰胺类化合物的合成及其生物活性

Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides

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